Patent GB-957841-A (GB)
Title: The preparation of organo-tin compounds and their use as catalysts in the productionof polymethanes
Inventor: HULSE RAE
IPC: C08G18/24
Filed: 1961-04-10
Abstract: The invention comprises organotin compounds of formula: [R1R2Sn(OH)x]mXn where R1 and R2 are the same or different alkyl aralkyl or cycloalkyl groups and X is the residue of an ortho dihydric phenol which may be attached by the hydroxyl oxygen atoms to one or two tin atoms, or the residue of a monohydric phenol having as an ortho substituent to the hydroxyl group an alkyl, aralkyl, cycloalkyl or dialkylaminoalkyl group, the dihydric or monohydric phenol having additional alkyl or dialkylaminoalkyl substituents in the ring if desired, x is 0 or 1, and when x is 0, m is 1 and n is 1 or 2, and in this case when n is 2, the X's may be derived from one monohydric phenol or two different monohydric phenols, and when x is 1, n is 1 and m is 1 or 2.  Examples of groups R1+R2 include alkyl groups such as isopropyl, n-butyl, n-hexyl and 2-ethylhexyl, aralkyl groups such as benzyl and phenylethyl and cycloalkyl groups such as cyclohexyl and methylcyclohexyl. Monohydric phenols specified include 2,6-di-tert.-butyl-4-methylphenol, 2-methyl-6-tert. butylphenol, tris-(a -methylbenzyl) phenol, 2-a -methylcyclohexyl-4, 6-dimethylphenol and 2, 4, 6-tris-(dimethylaminomethyl) phenol. Dihydric phenols specified include catechol, tert. butyl-catechol, pyrogallol, 2, 21-dihydroxy-3, 31-di-tert. octyl-5, 51-dimethyldiphenylethane, 2, 21-methylene bis(6-tert. butyl-p-cresol), 4, 41-methylene bis (2, 6-ditert. butyl phenol) and 4, 41-thiobis (6-tert-butyl-o-cresol). The tin oxide may be reacted with the phenol in the absence of a solvent or more conveniently in the presence of a hydrocarbon solvent such as benzene, light petroleum or toluene, preferably between 80 DEG C. and 120 DEG C. The compounds of the invention may be used as catalysts in the preparation of polyurethane resins (see Division C3). Specification 892,137 is referred to.ALSO:Rigid or flexible, cellular or homogeneous polyurethane products may be made by reacting hydroxyl group-containing polymers containing at least two isocyanate-reactive groups per molecule with organic polyisocyanates in the presence of an organotin compound of formula: [R1R2Sn(OH)x]mXn where R1 and R2 are the same or different alkyl, aralkyl or cycloalkyl groups and X is the residue of an orthodihydric phenol which may be attached by the hydroxyl oxygen atoms to one or two tin atoms, or the residue of a monohydric phenol having as an ortho substituent to the hydroxyl group an alkyl, aralkyl, cycloalkyl or dialkylaminoalkyl group, the dihydric or monohydric phenol having additional alkyl or dialkylaminoalkyl substituents in the ring if desired, x is 0 or 1, and when x is 0, m is 1 and n is 1 or 2, and in this case when n is 2, the x's may be derived from one monohydric phenol or two different monohydric phenols, and when x is 1, n is 1 and m is 1 or 2. The hydroxyl-containing polymer may be a polyester, polyesteramide or polyether or mixtures thereof. Lists of suitable polymers and organic isocyanates are given. Foamed products are obtained by carrying out the reaction in the presence of water and/or a low boiling point liquid e.g. a fluorinated alkane.  Tertiary amines (many specified) may be used as additional catalysts.  Surface active agents, flame retardants, plasticisers, fillers and antioxidants may also be incorporated in the compositions. Example 6 describes the preparation of polyurethane resins from adipic acid, glycerol, ethylene glycol and tolylene-2:4-diisocyanate in the presence of compounds of formulae: <FORM:0957841/C3/1> <FORM:0957841/C3/2> <FORM:0957841/C3/3> <FORM:0957841/C3/4> <FORM:0957841/C3/5> Example 7 describes the preparation of a cellular product from polypropylene glycol, a mixture of tolylene-2:4-diisocyanate and tolylene-2:6-diisocyanate, an aqueous solution of 4-dimethyl-aminopyridine and the compound of formula IV above. Specification 892,137 is referred to.ALSO:In Example 6, thin steel plates are coated with a polyurethane composition containing as catalysts organotin compounds as specified (see Division C3).